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Synthesis of Quaternary Amino Acids Bearing a (2‘Z)-Fluorovinyl α-Branch:  Potential PLP Enzyme Inactivators

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journal contribution
posted on 2004-05-27, 00:00 authored by David B. Berkowitz, Roberto de la Salud-Bea, Wan-Jin Jahng
Protected α-formyl amino acids, themselves available from the corresponding α-vinyl amino acids, are stereoselectively transformed into the (Z)-configured α-(2‘-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl α-fluoro-α-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-α-fluorovinyl sulfones and (E)-α-fluorovinylstannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds.

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